NP-MRD: Showing NP-Card for Cicholosumin E (NP0333673)

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Record Information

Version

2.0

Created at

2024-07-31 23:47:32 UTC

Updated at

2024-09-16 10:46:51 UTC

NP-MRD ID

NP0333673

Natural Product DOI

https://doi.org/10.57994/3152

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cicholosumin E

Description

Cicholosumin E belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Cicholosumin E was first documented in 2024 (PMID: 39032793). Based on a literature review very few articles have been published on Cicholosumin E.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 04152302212D          

 28 30  0  0  1  0            999 V2000
    4.3545    1.8612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8305    1.2239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1204    0.4515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6659   -0.2370    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2750    0.4895    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1803   -0.8820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9967   -1.6863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6417   -2.2007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2534   -2.0443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5101   -1.6863    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8651   -2.2007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9881   -3.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3431   -3.5308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5751   -3.2294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4660   -4.3466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2340   -4.6480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7560   -3.3179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3265   -0.8820    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8409   -0.2370    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3864    0.4515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5912    0.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5541   -0.5921    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7312   -0.6501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1774   -1.3261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9461    0.7464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9157    0.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9527   -0.5921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6412   -1.0466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
 10  9  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 12 17  2  0  0  0  0
 18 10  1  0  0  0  0
 18 19  1  1  0  0  0
 19  4  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 22 21  1  0  0  0  0
 18 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  1  0  0  0
 21 25  2  0  0  0  0
  3 26  2  0  0  0  0
 26 27  1  0  0  0  0
  6 27  1  0  0  0  0
 27 28  2  0  0  0  0
M  END


  Mrv2104 04152302212D          

 28 30  0  0  1  0            999 V2000
    4.3545    1.8612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8305    1.2239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1204    0.4515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6659   -0.2370    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2750    0.4895    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1803   -0.8820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9967   -1.6863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6417   -2.2007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2534   -2.0443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5101   -1.6863    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8651   -2.2007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9881   -3.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3431   -3.5308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5751   -3.2294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4660   -4.3466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2340   -4.6480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7560   -3.3179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3265   -0.8820    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8409   -0.2370    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3864    0.4515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5912    0.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5541   -0.5921    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7312   -0.6501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1774   -1.3261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9461    0.7464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9157    0.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9527   -0.5921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6412   -1.0466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
 10  9  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 12 17  2  0  0  0  0
 18 10  1  0  0  0  0
 18 19  1  1  0  0  0
 19  4  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 22 21  1  0  0  0  0
 18 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  1  0  0  0
 21 25  2  0  0  0  0
  3 26  2  0  0  0  0
 26 27  1  0  0  0  0
  6 27  1  0  0  0  0
 27 28  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0333673

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12[C@H]3OC(=O)[C@](C)(O)[C@@H]3[C@H](CC(C)=C1C(=O)C=C2CO)OC(=O)C(\C)=C/C

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O7/c1-5-9(2)18(23)26-13-6-10(3)14-12(22)7-11(8-21)15(14)17-16(13)20(4,25)19(24)27-17/h5,7,13,15-17,21,25H,6,8H2,1-4H3/b9-5-/t13-,15-,16+,17+,20+/m0/s1

> <INCHI_KEY>
UEYYBWBWYZYRBU-JVTHTGRESA-N

> <FORMULA>
C20H24O7

> <MOLECULAR_WEIGHT>
376.405

> <EXACT_MASS>
376.152203113

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
38.45953825450492

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,3aR,4S,9aS,9bR)-3-hydroxy-9-(hydroxymethyl)-3,6-dimethyl-2,7-dioxo-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_LOGP>
1.3333342486666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.947078691777794

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.204587883593495

> <JCHEM_PKA_STRONGEST_BASIC>
-2.760559473545233

> <JCHEM_POLAR_SURFACE_AREA>
110.13

> <JCHEM_REFRACTIVITY>
97.16169999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3R,3aR,4S,9aS,9bR)-3-hydroxy-9-(hydroxymethyl)-3,6-dimethyl-2,7-dioxo-3aH,4H,5H,9aH,9bH-azuleno[4,5-b]furan-4-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-APR-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-APR-23         0                                  
HETATM    1  O   UNK     0       8.128   3.474   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       7.150   2.285   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.691   0.843   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.843  -0.442   0.000  0.00  0.00           C+0
HETATM    5  H   UNK     0       6.113   0.914   0.000  0.00  0.00           H+0
HETATM    6  C   UNK     0       7.803  -1.646   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.461  -3.148   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.665  -4.108   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.073  -3.816   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.686  -3.148   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.482  -4.108   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.711  -5.631   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.507  -6.591   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.073  -6.028   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.737  -8.114   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.170  -8.676   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.145  -6.193   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.343  -1.646   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.303  -0.442   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.455   0.843   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.970   0.433   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.901  -1.105   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.365  -1.213   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.198  -2.475   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       1.766   1.393   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       9.176   0.433   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.245  -1.105   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      10.530  -1.954   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   26                                                  
CONECT    4    3    5    6   19                                             
CONECT    5    4                                                            
CONECT    6    4    7   27                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   18                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15                                                            
CONECT   17   12                                                            
CONECT   18   10   19   22                                                  
CONECT   19   18    4   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   25                                                  
CONECT   22   21   18   23   24                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   21                                                            
CONECT   26    3   27                                                       
CONECT   27   26    6   28                                                  
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₄O₇

Average Mass

376.4050 Da

Monoisotopic Mass

376.15220 Da

IUPAC Name

(3R,3aR,4S,9aS,9bR)-3-hydroxy-9-(hydroxymethyl)-3,6-dimethyl-2,7-dioxo-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl (2Z)-2-methylbut-2-enoate

Traditional Name

(3R,3aR,4S,9aS,9bR)-3-hydroxy-9-(hydroxymethyl)-3,6-dimethyl-2,7-dioxo-3aH,4H,5H,9aH,9bH-azuleno[4,5-b]furan-4-yl (2Z)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

[H][C@@]12[C@H]3OC(=O)[C@](C)(O)[C@@H]3[C@H](CC(C)=C1C(=O)C=C2CO)OC(=O)C(\C)=C/C

InChI Identifier

InChI=1S/C20H24O7/c1-5-9(2)18(23)26-13-6-10(3)14-12(22)7-11(8-21)15(14)17-16(13)20(4,25)19(24)27-17/h5,7,13,15-17,21,25H,6,8H2,1-4H3/b9-5-/t13-,15-,16+,17+,20+/m0/s1

InChI Key

UEYYBWBWYZYRBU-JVTHTGRESA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	weizheyang1002@126.com	XinJiang Technical Institute of Physics and Chemistry Chinese Academy of Sciences	Zheyang Wei	2024-07-31	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	weizheyang1002@126.com	XinJiang Technical Institute of Physics and Chemistry Chinese Academy of Sciences	Zheyang Wei	2024-07-31	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600.230706647, CD₃OD, simulated)	weizheyang1002@126.com	XinJiang Technical Institute of Physics and Chemistry Chinese Academy of Sciences	Zheyang Wei	2024-07-31	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
glandulosum		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Farsesane sesquiterpenoid
Sesquiterpenoid
Fatty alcohol ester
Fatty alcohol
Fatty acid ester
Fatty acyl
Alpha-branched alpha,beta-unsaturated-ketone
Gamma butyrolactone
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated ketone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Tertiary alcohol
Enone
Acryloyl-group
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.33	ChemAxon
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	110.13 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	97.16 m³·mol⁻¹	ChemAxon
Polarizability	38.46 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wei Z, Turak A, Li B, Aisa HA: Guaianolide sesquiterpene lactones from Cichorium glandulosum and their anti-neuroinflammation activities. Phytochemistry. 2024 Jul 19;226:114223. doi: 10.1016/j.phytochem.2024.114223. [PubMed:39032793 ]

Showing NP-Card for Cicholosumin E (NP0333673)

MOL for NP0333673 (Cicholosumin E)

3D MOL for NP0333673 (Cicholosumin E)

3D SDF for NP0333673 (Cicholosumin E)

3D-SDF for NP0333673 (Cicholosumin E)

PDB for NP0333673 (Cicholosumin E)

3D PDB for NP0333673 (Cicholosumin E)

SMILES for NP0333673 (Cicholosumin E)

INCHI for NP0333673 (Cicholosumin E)

Structure for NP0333673 (Cicholosumin E)

3D Structure for NP0333673 (Cicholosumin E)